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Azo compound and salt thereof

a technology of azo compound and salt, which is applied in the field of new dye type polarizing film, can solve the problems of insufficient heat resistance, insufficient durability, and generally insufficient initial polarization performance heat resistance, and achieve excellent polarization performance and high performan

Active Publication Date: 2007-12-04
NIPPON KAYAKU CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010]An object of the present invention is to provide a polarizing plate of high performance having excellent polarization performance and humidity resistance, heat resistance and light resistance.
[0011]Another object of the present invention is to provide a neutral color polarizing plate of high performance which is produced by adsorbing two or more kinds of dichromatic dyes in a polymeric film and orientating it, and which does not cause color leakage at cross position in the wavelength range (400 to 700 nm) of visible light, and furthermore which has excellent polarization performance and humidity resistance, heat resistance and light resistance.
[0012]A further object of the present invention is to provide polarizing plates of high performance corresponding to three primary colors for a color liquid crystal projector, which are good in all of brightness, polarization performance, durability and light resistance.
[0013]In order to attain such objects the present inventors have devoted themselves to research, and consequently have found that a polarizing film and a polarizing plate which contain a specific dye, has excellent polarization performance and humidity resistance, heat resistance and light resistance, and thus have accomplished the present invention.

Problems solved by technology

Among them, an iodine type polarizing film using iodine as a polarizing element is excellent in initial polarization performance but weak to water and heat, and has problem in its durability when it is used for a long time under the condition of high temperature and high humidity.
In order to improve durability, a method of treating an iodine type polarizing film with formalin or an aqueous solution containing boric acid, or using a polymeric film having a low moisture permeability as a protective film, or the like is considered, but its effect does not seem to be sufficient.
On the other hand, a dye type polarizing film using a dichromatic dye as a polarizing element is excellent in humidity resistance and heat resistance but generally not sufficient in initial polarization performance as compared with an iodine type polarizing film.
As mentioned above, an iodine type polarizing plate uses iodine as a polarizer and hence has a problem in that light resistance, heat resistance and wet heat resistance are not sufficient.
Therefore, transmittance of light is bad to the requirement of the marketplace that more brightness should be realized as in a color liquid crystal projector, and there is a problem that in order to realize brightness it is necessary to make light intensity at the source higher.
However, the conventional polarizing plates containing said water-soluble dyes have not yet satisfied the needs of the marketplace sufficiently from the viewpoint of polarization characteristics, absorption wavelength range, hue and the like.
In addition, Swiss Patent No. 326,553 discloses a trisazo compound having an unsubstituted triazole ring, but does not disclose a trisazo compound having a triazole ring with substituents.

Method used

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  • Azo compound and salt thereof
  • Azo compound and salt thereof
  • Azo compound and salt thereof

Examples

Experimental program
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Effect test

example 1

[0091]17.3 parts of 3-aminobenzenesulfonic acid was added to 500 parts of water, and dissolved with sodium hydroxide. Cooling was carried out to 10° C. or lower, 32 parts of 35% hydrochloric acid was added, then 6.9 parts of sodium nitrite was added, and stirring was carried out for 1 hour at 5 to 10° C. 18.8 parts of 2,4-diaminobenzenesulfonic acid was added thereto, sodium carbonate was added while stirring at 10 to 15° C. to make the pH 3, and further stirring was carried out to complete the coupling.

[0092]200 parts of 28% ammonia water and 125 parts of copper sulfate pentahydrate were added to this aqueous reaction product solution, and stirring was carried out for 0.5 hour at 80° C. to produce a triazole compound. To 37.0 parts of the resultant triazole compound were added 32 parts of 35% hydrochloric acid and then 6.9 parts of sodium nitrite respectively, and stirring was carried out for 2 hours at 25 to 30° C. 10.9 parts of 3-methylaniline dissolved in diluted aqueous hydroch...

example 2

[0097]Similarly to Example 1 except that the secondary coupler in the compound represented by the above formula (18) was changed to 13.7 parts of 2-methoxy-5-methylaniline from 12.1 parts of 2,5-dimethylaniline, there was obtained the sodium salt of a trisazo compound represented by the formula (3) previously cited. This compound salt expressed reddish violet. 20% aqueous pyridine solution of this compound salt had a maximum absorption wavelength of 566 nm as measured by a spectrophotometer (V-530 manufactured by JASCO Corporation).

example 3

[0098]Similarly to Example 1 except that there was used the disazo compound represented by the following formula (19) which was synthesized by changing the starting material to 21.7 parts of 2-amino-4-sulfo-benzoic acid from 17.3 parts of 3-aminobenzenesulfonic acid, there was obtained the sodium salt of a trisazo compound represented by the above formula (5).

[0099]

This compound salt expressed red. 20% aqueous pyridine solution of this compound salt had a maximum absorption wavelength of 544 nm as measured by a spectrophotometer (V-530 manufactured by JASCO Corporation).

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Abstract

The present invention relates to an azo compound represented by the following formula (1):wherein A denotes a phenyl group having 1 to 3 substituents such as sulfonic acid group, amino group, lower alkyl groups and lower alkoxyl groups, or a naphthyl group, B denotes hydrogen atom, sulfonic acid group, a lower alkyl group, a lower alkoxyl group or the like, each of R1 to R4 independently denotes hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxyl group or the like, D denotes —NHCO—, —N═N— or —NH—, E denotes hydrogen atom, a lower alkyl group or a phenyl group having 1 to 3 substituents such as hydroxyl group and amino group, n denotes 0 or 1, and m denotes 0 or 1, or a salt thereof, or a copper complex compound of either of them, which is used for a polarizing plate having excellent polarization performance and durability and furthermore little color leakage in visible light range.

Description

TECHNICAL FIELD[0001]The present invention relates to an azo compound and the salt thereof, and to a novel dye type polarizing film containing either of them.BACKGROUND ART[0002]A polarizing plate having function of transmitting and shielding light as well as a liquid crystal having switching function of light, serve as a fundamental constitutional element of a display device such as a liquid crystal display (LCD). Application field of this LCD has been expanded from initial small items such as electronic calculator and clock to a wide range of equipments such as portable personal computer, word processor, liquid crystal projector, liquid crystal television set, car navigation system, and indoor and outdoor measurement hardwares. Accordingly, because of use under broad conditions of low temperature to high temperature, low humidity to high humidity, and low light intensity to high light intensity, there has been demanded a polarizing plate having high polarization performance and ex...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C09B31/20C09B45/28F21V9/14G02B5/30C09B31/22C09B33/22C09B33/26
CPCC09B31/20C09B31/22G02B5/30C09B33/26C09B45/28C09B33/22C07D249/18
Inventor SADAMITSU, YUICHIKAWABE, KAZUYUKI
Owner NIPPON KAYAKU CO LTD
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